Light-resistive dispersant and ink composition containing the same

ABSTRACT

A 2-methoxyphenol derivative may be used as an ultraviolet (UV) light absorbing dispersant and, an ink composition may include the 2-methoxyphenol derivative as a light-resistant dispersant. The 2-methoxyphenol derivative absorbs UV light and thus provides light resistance to outputs. The 2-methooxyphenol derivative also improves dispersibility. When the 2-methoxyphenol derivative is used to prepare an ink composition, the ink composition has improved dispersibility and light resistance, and there is no need to add a light-resistant additive.

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the priority of Korean Patent ApplicationNo. 2002-80056, filed on Dec. 14, 2002, in the Korean IntellectualProperty Office, the disclosure of which is incorporated herein in itsentirety by reference.

BACKGROUND OF THE INVENTION

[0002] 1. Field of the Invention

[0003] The present invention relates to a light-resistant dispersant,and more particularly, to an ultraviolet (UV) light absorbing dispersantand an ink composition containing the same.

[0004] 2. Description of the Related Art

[0005] In general, ink compositions for ink-jet printing contain acolorant, a solvent, and an additive, such as a dispersant. A dye or apigment may be used for the colorant. However, when a dye is used as thecolorant, water resistance and light resistance are limited, whereaswhen a pigment is used as the colorant, water resistance and lightresistance are improved.

[0006] A common dispersant used in ink compositions is a polymerdispersant bearing hydrophilic and hydrophobic groups. The hydrophobicgroup of the polymer dispersant interacts with a colorant in the inkcomposition to stabilize dispersion of the colorant. The hydrophilicgroup of the polymer dispersant interacts with an aqueous solvent tooffer steric stability.

[0007] However, due to the large molecular weight of the polymerdispersant, the physical properties, for example, the viscosity, of thecomposition are greatly varied even when there is a minor change in theamount of the dispersant. Accordingly, it is difficult to adjust theamount of the additive used. In addition, although the polymerdispersant includes hydrophilic groups in its molecular structure, thehydrophilic fraction of the polymer with respect to the total amount ofthe composition is too small to sufficiently dissolve the compound inwater, and it takes more time to dissolve the hydrophilic fraction ofthe polymer.

[0008] After printing on media, such as paper, using the inkcomposition, the ink printed on the media is exposed to the air,moisture, and/or sunlight. Accordingly, an ink composition havingeffective light resistance and water resistance in such environments isrequired.

[0009] To improve the light resistance of ink compositions, a method ofadding a silicon-containing compound as a light-resistant additive tooffer a UV absorbing effect is suggested in U.S. Pat. No. 6,346,595.However, this silicone-containing compound is structurally complex, andthus has poor miscibility with other components of the ink composition,especially when it has a larger molecular weight.

SUMMARY OF THE INVENTION

[0010] The present invention provides a light-resistant dispersantproviding an improved ultraviolet (UV) light absorbing property anddispersibility.

[0011] The present invention also provides an ink composition containingthe above light-resistant dispersant, which has improved lightresistance and dispersibility.

[0012] In one aspect, the present invention provides a 2-methoxyphenolderivative having formula (1) below:

[0013] where X is selected from among a substituted or unsubstitutedC₁-C₃₀ alkylene group, a substituted or unsubstituted C₂-C₃₀ alkenylenegroup, a substituted or unsubstituted C₂-C₃₀ alkynylene group, asubstituted or unsubstituted C₆-C₃₀ arylene group, a substituted orunsubstituted C₇-C₃₀ arylalkylene group, a substituted or unsubstitutedC₁-C₃₀ heteroalkylene group, a substitute or unsubstituted C₂-C₃₀heteroarylene group, and a substituted or unsubstituted C₃-C₃₀heteroarylalkylene group;

[0014] Y is selected from among —O—, —NR—, —N(H)═N(H)—, —S—, —P—,—C(═O)—NR—, —NR—C(═O)—, —S(═O)(═O)O—, —C(═O)O—, —O—C(═O)—, —P(═O)O—,—C(═O)—O—C(═O)—, —C(═O)—S—C(═O)—, —C(═O)—NR—C(═O)—, —C(═NH)—O—C(═NH)—,—C(═S)—O—C(═S)—, —C(═NH)—NR—C(═NH)—, —C(═S)—NR—C(═S)—,—C(═NH)—S—C(═NH)—, and —C(═S)—S—C(═S)—, where R is a hydrogen atom or aC₁-C₅ alkyl group; and

[0015] Z is one of a group having the formula of—(CH₂CH₂O)_(a)—(CH₂CH(CH₃)O)_(b)—(CH₂CH₂O)_(c)—H where a, b, and c areindependently integers from 1 to 20 and a group having formula (2)below:

[0016] where R₃ and R₄ are independently C₁-C₁₀ alkyl groups; R₅ and R₆are independently a hydrogen atom or a methyl group; R₇ is selected fromamong a C₁-C₃₀ alkylene group, a C₂-C₃₀ alkenylene group, C₂-C₃₀alkynylene group, a C₆-C₃₀ arylene group, a C₇-C₃₀ arylalkylene group, aC₁-C₃₀ heteroalkylene group, a C₂-C₃₀ heteroarylene group, and a C₃-C₃₀heteroarylalkylene group, which have a terminal group selected fromamong a phosphorc acid or a salt thereof, a phosphoric acid or a saltthereof, a sulfonic acid or a salt thereof, —OH, and —NH₂; and m and nare independently real numbers from 1 to 10 where m+n≧2.

[0017] In another aspect, the present invention provides an inkcomposition containing the 2-methoxyphenol derivative of formula (1), anaqueous medium, and a colorant. The amount of the 2-methoxyphenolderivative may be in the range of 0.1-20 parts by weight with respect to100 parts by weight of the ink composition.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0018] A 2-methoxyphenol derivative having formula (1) according to anembodiment of the present invention will be described in detail.

[0019] In formula (1) above, the 2-methoxyphenol ring and X areanchoring groups that improve reactivity, for example, chemicalaffinity, with a pigment used as a colorant, Y is a junction group, andZ is a stabilizing group that facilitates dispersion of a pigment in asolvent.

[0020] X in formula (1) is selected from among a substituted orunsubstituted C₁-C₃₀ alkylene group, a substituted or unsubstitutedC₂-C₃₀ alkenylene group, a substituted or unsubstituted C₂-C₃₀alkynylene group, a substituted or unsubstituted C₆-C₃₀ arylene group, asubstituted or unsubstituted C₇-C₃₀ arylalkylene group, a substituted orunsubstituted C₁-C₃₀ heteroalkylene group, a substitute or unsubstitutedC₂-C₃₀ heteroarylene group, and a substituted or unsubstituted C₃-C₂₀heteroarylalkylene group.

[0021] Examples of an unsubstituted C₁-C₃₀ alkylene group for X informula (1) include, but are not limited to, a methylene group, anethylene group, a propylene group, an isopropylene group, a sec-butylenegroup, a pentylene group, an iso-amylene group, and a hexylene group,wherein at least one hydrogen atom in the alkylene group may besubstituted with a halogen atom, a hydroxy group, a nitro group, a cyanogroup, an amino group, an amidino group, hydrazine, hydazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ heteroalkyl group, aC₆-C₂₀ aryl group, a C₇-C₂₀ arylalkyl group, a C₂-C₂₀ heteroaryl group,or a C₃-C₂₀ heteroarylalkyl group.

[0022] An unsubstituted C₂-C₃₀ alkenylene or alkynylene group for X informula (1) includes a carbon double or triple bond in the middle or atthe end of the alkylene group defined above. Examples of such anunsubstituted C₁-C₃₀alkenylene or alkynylene group include ethylene,propylene, butylene, hexylene, acetylene, and the like. At least onehydrogen atom in the alkenylene or alkynylene group may be substitutedwith a halogen atom, a hydroxy group, a nitro group, a cyano group, anamino group, an amidino group, hydrazine, hydazone, a carboxyl group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenylgroup, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ heteroalkyl group, a C₆-C₂₀ arylgroup, a C₇-C₂₀ arylalkyl group, a C₂-C₂₀ heteroaryl group, or a C₃-C₂₀heteroarylalkyl group.

[0023] A heteroalkylene group for X in formula (1) includes a nitrogenatom, sulfur atom, oxygen atom, or phosphorous atom in the alkylenegroup defined above. Examples of such a heteroalkylene group include amethoxy group, an ethoxy group, a propoxy group, a butoxy group, at-butoxy group, and the like. Examples of a heteroalkylene group with asubstituent include haloalkoxy radicals, such as fluoromethoxy,chloromethoxy, trifluoromethoxy, trifluoroethoxy, fluoroethoxy,fluoropropoxy, and the like. At least one hydrogen atom in theheteroalkylene group may be substituted with a halogen atom, a hydroxygroup, a nitro group, a cyano group, an amino group, an amidino group,hydrazine, hydazone, a carboxyl group or a salt thereof, a sulfonic acidgroup or a salt thereof, a phosphoric acid group or a salt thereof, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkenyl group, a C₁-C₂₀alkynyl group, aC₁-C₂₀ heteroalkyl group, a C₆-C₂₀ aryl group, a C₇-C₂₀ arylalkyl group,a C₆-C₂₀ heteroaryl group, or a C₆-C₂₀ heteroarylalkyl group.

[0024] An arylene group for X in formula (1), which may be used alone orin combination, refers to a C₆-C₃₀ carbocyclic system containing atleast one ring wherein such rings may be attached together in a pendentmanner or may be fused. The term “aryl” implies aromatic radicals, suchas phenyl, naphthyl, tetrahydronaphthyl, indane, biphenyl, and the like.The arylene group may have a substituent, such as hydroxy, halo,haloalkyl, nitro, cyano, alkoxy, lower alkylamino, and the like. Atleast one hydrogen atom in the arylene group may be substituted with ahalogen atom, a hydroxy group, a nitro group, a cyano group, an aminogroup, an amidino group, hydrazine, hydazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkenyl group, aC₁-C₂₀ alkynyl group, a C₁-C₂₀ heteroalkyl group, a C₆-C₂₀ aryl group, aC₇-C₂₀ arylalkyl group, a C₆-C₂₀ heteroaryl group, or a C₆-C₂₀heteroarylalkyl group.

[0025] An arylalkylene group for X in formula (1) refers to theabove-defined arylene group having lower alkyl substitute radicals, forexample, methyl, ethyl, propyl, and the like, for some hydrogen atoms.Examples of such an arylalkylene group include benzyl, phenylethyl, etc.At least one hydrogen atom in the arylalkylene group may be substitutedwith a halogen atom, a hydroxy group, a nitro group, a cyano group, anamino group, an amidino group, hydrazine, hydazone, a carboxyl group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkenylgroup, a C₁-C₂₀ alkynyl group, a C₁-C₂₀ heteroalkyl group, a C₆-C₂₀ arylgroup, a C₇-C₂₀ arylalkyl group, a C₆-C₂₀ heteroaryl group, or a C₆-C₂₀heteroarylalkyl group.

[0026] A heteroarylene group for X in formula (1) refers to a divalentcyclic system containing one, two, or three hetero atoms selected fromthe group consisting of N, O, P, and S. At least one hydrogen atom inthe heteroarylene group may be substituted with a halogen atom, ahydroxy group, a nitro group, a cyano group, an amino group, an amidinogroup, hydrazine, hydazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynylgroup, a C₁-C₂₀ heteroalkyl group, a C₆-C₂₀ aryl group, a C₇-C₂₀arylalkyl group, a C₆-C₂₀ heteroaryl group, or a C₇-C₂₀ heteroarylalkylgroup.

[0027] A heteroarylalkylene group for X in formula (1) refers to theabove-defined heteroarylene group having alkylene groups. At least onehydrogen atom in the heteroarylalkylene group may be substituted with ahalogen atom, a hydroxy group, a nitro group, a cyano group, an aminogroup, an amidino group, hydrazine, hydazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkenyl group, aC₁-C₂₀ alkynyl group, a C₁-C₂₀ heteroalkyl group, a C₆-C₂₀ aryl group, aC₇-C₂₀ arylalkyl group, a C₆-C₂₀ heteroaryl group, or a C₆-C₂₀heteroarylalkyl group.

[0028] In formula (1) above, Y is selected from among —O—, —NR—,—N(H)=N(H)—, —S—, —P—, —C(═O)—NR—, —NR—C(═O)—, —S(═O)(═O)O—, —C(═O)O—,—O—C(═O)—, —P(═O)O—, —C(═O)—O—C(═O)—, —C(═O)—S—C(═O)—, —C(═O)—NR—C(═O)—, —C(═NH)—O—C(═NH)—, —C(═S)—O—C(═S)—, —C═(NH)—N R—C(═NH)—,—C(═S)—NR—C(═S)—, —C(═NH)—S—C(═NH)—, and —C(═S)—S—C(═S)—, where R is ahydrogen atom or a C₁-C₅alkyl group.

[0029] In formula (1) above, Z is one of a group having the formula of—(CH₂CH₂O)_(a)—(CH₂CH(CH₃)O)_(b)—(CH₂CH₂O)_(c)—H where a, b, and c areindependently integers from 1 to 20 and a group having formula (2)below:

[0030] where R₃ and R₄ are different C₁-C₁₀ alkyl groups; R₅ and R₆ areindependently a hydrogen atom or a methyl group; R₇ is selected fromamong a C₁-C₃₀alkylene group, a C₂-C₃₀ alkenylene group, C₂-C₃₀alkynylene group, a C₆-C₃₀ arylene group, a C₇-C₃₀ arylalkylene group, aC₁-C₃₀ heteroalkylene group, a C₂-C₃₀ heteroarylene group, and a C₃-C₃₀heteroarylalkylene group, which have a terminal group selected fromamong a carboxylic acid or a salt thereof, a phosphoric acid or a saltthereof, a sulfonic acid or a salt thereof, —OH, and —NH₂; and m and nare real numbers from 1 to 10 where m+n≧2.

[0031] The 2-methoxyphenol derivative of formula (1) according to anembodiment of the present invention absorbs UV light and providesdispersibility. Accordingly, when 2-methoxyphenol is added to an inkcomposition, the light resistance and dispersibility of the inkcomposition are improved.

[0032] An ink composition according to an embodiment of the presentinvention that contains the above-described 2-methoxyphenol derivativeof formula (1) will now be described in detail.

[0033] An ink composition according to an embodiment of the presentinvention includes an aqueous medium, a colorant, and the2-methoxyphenol derivative of formula (1) acting as a light-resistantdispersant. The ink composition according to an embodiment of thepresent may contain 0.1-20 parts by weight of the compound of formula(1) with respect to 100 parts by weight of the ink composition.

[0034] Water may be used alone for the aqueous medium of the inkcomposition according to an embodiment of the present invention.Alternatively, a mixture of water and at least one organic solvent maybe used for the aqueous medium. In this case, the amount of the organicsolvent may be in the range of 2-50 parts by weight with respect to 100parts by weight of the aqueous medium. The viscosity and surface tensionof the ink composition may be adjusted within an appropriate range usingan organic solvent in the aqueous medium.

[0035] Examples of the organic solvent include, but are not limited to,alcohols, such as methyl alcohol, ethyl alcohol, n-propyl alcohol,isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, t-butyl alcohol,isobutyl alcohol, etc.; ketones, such as acetone, methylethyl ketone,diacetone alcohol, etc.; esters, such as ethyl acetate, ethyl lactate,etc.; polyhydric alcohols, such as ethylene glycol, diethylene glycol,triethylene glycol, propylene glycol, butylene glycol, 1,4-butane diol,1,2,4-butane triol, 1,5-pentane diol, 1,2-hexane diol, 1,6-hexane diol,1,2,6-hexane triol, hexylene glycol, glycerol, glycerol ethoxylate,trimethylolpropane ethoxylate, etc.; lower alkyl ethers, such asethylene glycol monomethyl ether, ethylene glycol monoethyl ether,diethylene glycol methyl ether, diethylene glycol ethyl ether,diethylene glycol methyl ether, diethylene glycol ethyl ether,triethylene glycol monomethyl ether, triethylene glycol monoethyl ether,etc.; nitrogen-containing compounds, such as 2-pyrrolidone,N-methyl-2-pyrrolidone, caprolactam, etc.; and sulfur-containingcompounds, such as dimethyl sulfoxide, tetramethylene sulfone,thioglycol, etc.

[0036] The ink composition according to an embodiment of the presentinvention may further include an additive, for example, a viscosityadjuster, a surfactant, a storage stabilizer, or a wetting agent.

[0037] The viscosity adjuster of the ink composition ensures a smootherjetting process through viscosity adjustment. Examples of the viscosityadjuster that may be used in an embodiment of the present inventioninclude polyvinyl alcohol, casein, carboxymethylcellulose, etc. Theamount of the viscosity adjuster may be in the range of 0.1-5.0 parts byweight with respect to 100 parts by weight of the total weight of2-methoxy phenol derivative, an aqueous medium, and a colorant.

[0038] The surfactant of the ink composition controls the surfacetension of the ink composition. An anionic surfactant, cationicsurfactant or a nonionic surfactant may be used for the surfactant. Inparticular, the surfactant of the ink composition stabilized wettabilitywhen the composition is sprayed via a nozzle. The amount of thesurfactant may be in the range of 0.1-5.0 parts by weight with respectto 100 parts by weight of the ink composition.

[0039] The wetting agent of the ink composition prevents nozzles frombeing clogged with the ink composition. Examples of the wetting agentinclude polyhydric alcohols, in particular, glycerin, ethylene glycol,diethylene glycol, triethylene glycol, propylene glycol, dipropyleneglycol, hexylene glycol, 1,3-butanediol, 1,4-butanediol,1,5-pentanediol, 1,2-hexanediol, 1,6-hexanediol, 2-butene-1,4-diol,2-methyl-2-pentanediol, and a mixture of the foregoing alcohols. Theamount of the wetting agent may be in the range of 2-40 parts by weightwith respect to 100 parts by weight of the total weight of 2-methoxyphenol derivative, an aqueous medium, and a colorant.

[0040] The ink composition according to an embodiment of the presentinvention uses a disperse dye or pigment for the colorant. Specificexamples of the disperse dye include, but are not limited to, DISPERSEYELLOW 3, DISPERSE YELLOW 54, DISPERSE YELLOW 82, DISPERSE RED 60,DISPERSE RED 375, DISPERSE VIOLET 17, DISPERSE RED 4, DISPERSE RED 11,DISPERSE BLUE 60, DISPERSE BLUE 359, DISPERSE BLUE 14, DISPERSE BLUE 3,DISPERSE BLUE 72, DISPERSE BLUE 56. Specific examples of the pigmentinclude, but are not limited to, carbon black, graphite, vitreouscarbon, activated charcoal, activated carbon, anthraquinone,phthalocyanine blue, phthalocyanine green, diazos, monoazos,pyranthrones, perylene, quinacridone, and indigoid pigments.

[0041] The amount of the colorant may be in the range of 0.1-20 parts byweight, preferably, 0.5-15 parts by weight, with respect to 100 parts byweight of the ink composition.

[0042] The ink composition of an embodiment of the present invention mayfurther include an acid or a base to increase the solubility of thedispersant in a solvent and stabilize the dispersion of the pigment.

[0043] The above ink composition according to an embodiment of thepresent invention may be prepared as follow. Initially, the2-methoxyphenol derivative of formula (1) above acting as alight-resistant dispersant, a colorant, and additionally additives suchas a viscosity adjuster and a surfactant are added to an aqueous mediumand thoroughly mixed using a stirrer to homogenize. The resultantmixture is passed through a filter to provide an ink compositionaccording to an embodiment of the present invention.

[0044] The 2-methoxyphenol derivative of formula (1) according to anembodiment of the present invention may be used for, but is not limitedto, toner compositions, various paints, coating solutions, and the like,in addition to ink compositions.

[0045] The present invention will be described in greater detail withreference to the following examples. The following examples are forillustrative purposes and are not intended to limit the scope of theinvention. Although the following examples are described with referenceto ink compositions containing the 2-methoxyphenol derivative of formula(1), it will be appreciated that the present invention is not limited tothe ink compositions recited and that experimental methods used toevaluate the properties of the ink compositions may be applied to wettoners, dry toners, paints, and coating solutions.

SYNTHETIC EXAMPLE 1

[0046] 16.42 g of 2-methoxy-4-(1-prophenyl)phenol and 16.40 g of analkoxylated alcohol having formula (3) below were reacted in thepresence of an acidic or basic catalyst to provide 22.97 g of a compoundhaving formula (4) below.

HO—CH₂CH₂O—CH₂CH(CH₃)O—CH₂CH₂OH  (3)

SYNTHESIS EXAMPLE 2

[0047] 11.81 g of succinic acid was reacted with 16.40 g of thealkoxylated alcohol having formula 3 above in the presence of an acidiccatalyst (HCl or H₂SO₄). 18.96 g of 4-hydroxy-3-methoxybenzylaminehydrochloride was added to the reaction product and reacted in thepresence of SOCl₂ to provide 28.12 g of a compound having formula (5)below.

SYNTHESIS EXAMPLE 3

[0048] 11.81 g of succinic acid was reacted with 16.40 g of thealkoxylated alcohol having formula 3 above in the presence of an acidiccatalyst (HCl or H₂SO₄). 18.02 g of4-(3-hydroxyl-1-propenyl)-2-methoxyphenol was added to the reactionproduct and reacted in the presence of an acidic catalyst to provide29.83 g of a compound having formula (6) below.

SYNTHESIS EXAMPLE 4

[0049] (1) 100 mL of chloroform was placed in a 250-mL round-bottomedflask and bubbled while supplying a HCl gas for 1-2 hours. 29.5 g of2-methoxy-4-(2-propenyl)phenol was added into the flask, refluxed for 6hours or longer, and concentrated to provide 27.5 g of a crystallinecompound (A).

[0050] (2) 6.9 g of the crystalline compound (A) was dissolved in 100 mLof dimethylsulfoxide (DMSO). 37.3 g of an alkoxylated alcohol havingformula (7) below was added to the solution, reacted at 120° C. for 8hours or longer, and concentrated to provide a solution (B). Thissolution (B) was dissolved in ether and washed with distilled waterseveral times to extract the ether phase. This ether phase wasreconcentrated to provide 22.2 g of a compound having formula (8) below.

HO—(CH₂CH₂O)₅—(CH₂CH(CH₃)O)₇—(CH₂CH₂O)₅—H  (7)

SYNTHESIS EXAMPLE 5

[0051] (1) 129.6 g of the alkoxylated alcohol of formula (7) above and17.8 g of succinic acid were dissolved in 150 mL of ethyl acetatecontained in a 250-mL round-bottomed flask. 30 mL of concentratedsulfuric acid was slowly added together with one or two boiling chipsinto the solution and refluxed for 12 hours or longer. The reactionsolution was washed with distilled water to extract the organic phase.This organic phase was concentrated to provide 88.4 g of a crystallinecompound (C).

[0052] (2) 4.6 g of 4-hydroxyl-3-methoxybenzylamine hydrochloride and3.3 g of SOCl₂ were dissolved in 50 mL of DMSO contained in a 250-mLErlenmeyer flask and reacted at room temperature for 3 hours or longerto provide a solution (D). A solution of 27.6 g of the crystallinecompound (C) in 100 mL of DMSO was added to the solution (D) togetherwith one or two boiling chips and refluxed for 6 hours or longer.

[0053] The reaction solution was cooled to room temperature, and excessmethanol was added to precipitate a crystalline compound (E), followedby suction filtration. To remove the unreacted reactant, the crystallinecompound (E) was dissolved in DMSO, and methanol was added to thesolution to precipitate it again. The precipitant was collected using asuction filter and dried in an oven to provide 15.2 g of a compoundhaving formula (9) below.

SYNTHESIS EXAMPLE 6

[0054] 4.3 g of 4-(3-hydroxyl-1-propenyl)-2-methoxyphenol and 27.1 g ofthe crystalline compound (C) obtained in Synthesis Example 5 weredissolved in 100 mL of ethyl acetate contained in a 250-mLround-bottomed flask. 15 mL of concentrated sulfuric acid was slowlyadded together with one or two boiling chips into the solution andrefluxed for 10 hours or longer. The reaction solution was washed withdistilled water to extract the organic phase. This organic phase wasconcentrated to provide 13.7 g of a compound having formula (10) below.

SYNTHESIS EXAMPLE 7

[0055] 17.5 g of a compound having formula (12) was synthesized in thesame manner as in (2) of Synthesis Example 4, except that 31.9 g of analkoxylated alcohol having formula (11) below and 7.2 g of thecrystalline compound (A) obtained in Synthesis Example 4 were used.

HO—(CH₂CH₂O)₃—(CH₂CH(CH₃)O)₄—(CH₂CH₂O)₈—H  (11)

SYNTHESIS EXAMPLE 8

[0056] (1) 78.2 g of a crystalline compound (F) was synthesized in thesame manner as in (1) of Synthesis Example 5, except that 112.3 g of thealkoxylated alcohol of formula (11) above and 18.1 g of succinic acidwere used.

[0057] (2) 12.5 g of a compound having formula (13) below wassynthesized in the same manner as in Synthesis Example 6, except that4.3 g of 4-(3-hydroxyl-1-propenyl)-2-methoxyphenol and 23.4 g of thecrystalline compound (F) were used.

SYNTHESIS EXAMPLE 9

[0058] 22.5 g of an acrylate copolymer (having a weight averagemolecular weight of 1500) having formula (14) below and 2.7 g of4-(3-hydroxyl-1-propenyl)-2-methoxyphenol were dissolved in 50 mL ofethyl acetate contained in a 100-mL round-bottomed flask. 7 mL ofconcentrated sulfuric acid was slowly dropped together with one or twoboiling chips into the solution and refluxed for 12 hours or longer.

[0059] The resulting reaction solution was slowly added to 50 mL ofether contained in a 200-mL Erlenmeyer flask to precipitate acrystalline compound. This crystalline compound was collected using asuction filter and dried to provide 13.5 g of a compound having formula(15) below. In formula (14) below, m=9 and n=4.5.

SYNTHESIS EXAMPLE 10

[0060] 24.2 g of the crystalline compound (F) obtained in (1) ofSynthesis Example 8 was dissolved in 50 mL of DMSO contained in a 250-mLErlenmeyer flask. 5.2 g of SOCl₂ was added to the solution and reactedat room temperature for 1 hour or longer to provide a solution (G). Asolution of 5.8 g of a 2-methoxyphenol derivative having formula (16)below in 50 mL of DMSO was added to the solution (G) together with oneor two boiling chips and refluxed at 80° C. for 6 hours or longer. Theresulting reaction solution was cooled to room temperature, and excessmethanol was added to precipitate a crystalline compound, followed bysuction filtration. To remove the unreacted reactant, the crystallinecompound was dissolved in DMSO, and methanol was added to the solutionto precipitate it again. The precipitant was collected using a suctionfilter and dried to provide 16.8 g of a compound having formula (17)below.

SYNTHESIS EXAMPLE 11

[0061] 18.2 g of a compound having formula (19) below was synthesized inthe same manner as in Synthesis Example 10, except that 27.0 g of thecrystalline compound (C) obtained in Synthesis Example 5 and 7.8 g of a2-methoxyphenol derivative having formula (18) below were used.

SYNTHESIS EXAMPLE 12

[0062] 16.1 g of a compound having formula (21) below was synthesized inthe same manner as in Synthesis Example 6, except that 23.4 g of thecrystalline compound (F) obtained in (1) of Synthesis Example 8 and 7.1g of a 2-methoxyphenol derivative having formula (20) below were used.

SYNTHESIS EXAMPLE 13

[0063] 15.6 g of a compound having formula (23) below was synthesized inthe same manner as in Synthesis Example 6, except that 7.6 g of a2-methoxyphenol derivative having formula (22) below and 22.0 g of thealkoxylated alcohol of formula (11) above were used.

SYNTHESIS EXAMPLE 14

[0064] 15.6 g of a compound having formula (24) below was synthesized inthe same manner as in Synthesis Example 9, except that 2.9 g of the2-methoxyphenol derivative having formula (16) above and 22.5 g of theacrylate copolymer having formula (14) above were used. In formula (24)below, m=9, and n=4.5.

EXAMPLE 1

[0065] The following components were mixed while stirring for 30 minutesor longer to homogenize. The mixture was passed through a filter toprovide an ink composition. COMPONENT CONTENT Colorant (Carbon black) 4.0 g Water 73.0 g Isopropyl alcohol  3.0 g Glycerin  8.0 g Ethyleneglycol  8.0 g Compound of formula 4  4.0 g

EXAMPLES 2-14

[0066] Ink compositions were prepared in the same manner as in Example1, except that the compounds of formulae (5), (6), (8), (9), (10), (12),(13), (15), (17), (19), (21), (23), and (24) were respectively usedinstead of the compound of formula (4).

COMPARATIVE EXAMPLES 1-5

[0067] Ink compositions were prepared in the same manner as in Example1, except that TEGO dispers 750W, TEGO wet 260, a styrene-acrylic acidcopolymer, arylamine/styrenesulfonic acid copolymer, and a4-vinylpyrridine/maleic acid copolymer were respectively used instead ofthe compound of formula (4), 0.5 g of IRGANOX 245DW (available from CIBACO.) was further added, and the amount of water was reduced by 0.5 g.

[0068] The properties of the ink compositions prepared in Examples 1through 14 and Comparative Examples 1 through 5 were evaluated asfollows.

[0069] (1) Storage Stability

[0070] 100 mL of samples of the ink compositions prepared in Examples 1through 14 and Comparative Examples 1 through 5 were portioned intorespective heat-resistant glass bottles. The glass bottles were sealedand stored in a 60° C.-convection oven for 2 months. It was observedwhether precipitates appeared in the bottles. The results are shown inTable 1. In Table 1, ◯ indicates that no precipitate appears, and ×indicates that precipitates appear.

[0071] (2) Light Resistance

[0072] Ink cartridges (available from SAMSUNG ELECTRONICS CO.) werefilled with the respective ink compositions of Examples 1 through 14 andComparative Examples 1 through 5. After printing 2×2 cm solid patternsusing the ink cartridges, the printed results were exposed to light for100 hours in a Q-SUN XENON TEST CHAMBER. Optical density (OD) wasmeasured before and after light exposure, and A values were calculatedusing the following equation. Light resistance was evaluated as good (◯)for A 90, moderate (Δ) for 75 A<90, and poor (×) for A<75. The resultsare shown in Table 2.

A=OD after test/OD before test×100(%) TABLE 1 Comparative ExampleExample No. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 1 2 3 4 5 Result ◯ ◯ ◯ ◯ ◯◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯ X X X X X

[0073] TABLE 2 Comparative Example Example No. 1 2 3 4 5 6 7 8 9 10 1112 13 14 1 2 3 4 5 Result ◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯ ◯ Δ Δ ◯ Δ

[0074] As described above, a 2-methoxyphenol derivative having formula(1) above according to an embodiment of the present invention absorbs UVlight and thus provides light resistance to outputs. In addition, the2-methoxyphenol derivative improves dispersibility. Therefore, thecompound of formula (1) is used as a light-resistant dispersant in inkcompositions. When the 2-methoxyphenol derivative is used to prepare anink composition, the ink composition has improved dispersibility andlight resistance, and there is no need to add a light-resistantadditive.

[0075] While the present invention has been particularly shown anddescribed with reference to exemplary embodiments thereof, it will beunderstood by those of ordinary skill in the art that various changes inform and details may be made therein without departing from the spiritand scope of the present invention as defined by the following claims.

What is claimed is:
 1. A 2-methoxyphenol derivative having formula (1)below:

where X is selected from the group consisting of a substituted orunsubstituted C₁-C₃₀ alkylene group, a substituted or unsubstitutedC₂-C₃₀ alkenylene group, a substituted or unsubstituted C₂-C₃₀alkynylene group, a substituted or unsubstituted C₆-C₃₀ arylene group, asubstituted or unsubstituted C₇-C₃₀ arylalkylene group, a substituted orunsubstituted C₁-C₃₀ heteroalkylene group, a substituted orunsubstituted C₂-C₃₀ heteroarylene group, and a substituted orunsubstituted C₃-C₃₀ heteroarylalkylene group; Y is selected from thegroup consisting of —O—, —NR—, —N(H)=N(H)—, —S—, —P—, —C(═O)—NR—,—NR—C(═O)—, —S(═O)(═O)O—, —C(═O)O—, —O—C(═O)—, —P(═O)O—,—C(═O)—O—C(═O)—, —C(═O)—S—C(═O)—, —C(═O)—NR—C(═O)—, —C═(NH)—O—C(═NH)—,—C(═S)—O—C(═S)—, —C(═NH)—NR—C(═NH)—, —C(═S)—NR—C(═S)—,—C(═NH)—S—C(═NH)—, and —C(═S)—S—C(═S)—, where R is a hydrogen atom or aC₁-C₅ alkyl group; and Z is selected from the group consisting of agroup having the formula of—(CH₂CH₂O)_(a)—(CH₂CH(CH₃)O)_(b)—(CH₂CH₂O)_(c)—H where a, b, and c areindependently integers from 1 to 20 and a group having formula (2)below:

where R₃ and R₄ are independently C₁-C₁₀ alkyl groups; R₅ and R₆ areindependently a hydrogen atom or a methyl group; R₇ is selected from thegroup consisting of a C₁-C₃₀ alkylene group, a C₂-C₃₀ alkenylene group,a C₂-C₃₀ alkynylene group, a C₆-C₃₀ arylene group, a C₇-C₃₀ arylalkylenegroup, a C₁-C₃₀ heteroalkylene group, a C₂-C₃₀ heteroarylene group, anda C₃-C₃₀ heteroarylalkylene group, which have a terminal group selectedfrom the group consisting of a phosphorc acid or a salt thereof, aphosphoric acid or a salt thereof, a sulfonic acid or a salt thereof,—OH, and —NH₂; and m and n are independently real numbers from 1 to 10where m+n≧2.
 2. An ink composition comprising: the 2-methoxyphenolderivative having formula (1) below:

where X is selected from the group consisting of a substituted orunsubstituted C₁-C₃₀ alkylene group, a substituted or unsubstitutedC₂-C₃₀ alkenylene group, a substituted or unsubstituted C₂-C₃₀alkynylene group, a substituted or unsubstituted C₆-C₃₀ arylene group, asubstituted or unsubstituted C₇-C₃₀ arylalkylene group, a substituted orunsubstituted C₁-C₃₀ heteroalkylene group, a substituted orunsubstituted C₂-C₃₀ heteroarylene group, and a substituted orunsubstituted C₃-C₃₀ heteroarylalkylene group; Y is selected from thegroup consisting of —O—, —NR—, —N(H)═N(H)—, —S—, —P—, —C(═O)—NR—,—NR—C(═O)—, —S(═O)(═O)O—, —C(═O)O—, —O—C(═O)—, —P(═O)O—,—C(═O)—O—C(═O)—, —C(═O)—S—C(═O)—, —C(═O)—N R—C(═O)—, —C═(NH)—O—C(═NH)—,—C(═S)—O—C(═S)—, —C(═N H)—N R—C(═N H)—, —C(═S)—NR—C(═S)—,—C(═NH)—S—C(═NH)—, and —C(═S)—S—C(═S)—, where R is a hydrogen atom or aC₁-C₅ alkyl group; and Z is selected from the group consisting of agroup having the formula of—(CH₂CH₂O)_(a)—(CH₂CH(CH₃)O)_(b)—(CH₂CH₂O)_(c)—H where a, b, and c areindependently integers from 1 to 20 and a group having formula (2)below:

where R₃ and R₄ are independently C₁-C₁₀ alkyl groups; R₅ and R₆ areindependently a hydrogen atom or a methyl group; R₇ is selected from thegroup consisting of a C₁-C₃₀ alkylene group, a C₂-C₃₀ alkenylene group,a C₂-C₃₀ alkynylene group, a C₆-C₃₀ arylene group, a C₇-C₃₀ arylalkylenegroup, a C₁-C₃₀ heteroalkylene group, a C₂-C₃₀ heteroarylene group, anda C₃-C₃₀ heteroarylalkylene group, which have a terminal group selectedfrom the group consisting of a phosphorc acid or a salt thereof, aphosphoric acid or a salt thereof, a sulfonic acid or a salt thereof,—OH, and —NH₂; and m and n are independently real numbers from 1 to 10where m+n≧2; an aqueous medium; and a colorant.
 3. The ink compositionof claim 2, wherein an amount of the 2-methoxyphenol derivative is in arange of 0.1-20 parts by weight with respect to 100 parts by weight ofthe ink composition.
 4. The ink composition of claim 2, wherein theaqueous medium is water or a mixture of water and an organic solvent. 5.The ink composition of claim 4, wherein the amount of the organicsolvent in the aqueous medium is in a range of 2-50 parts by weight withrespect to 100 parts by weight of the aqueous medium.
 6. The inkcomposition of claim 4, wherein the organic solvent is at least oneselected from the group consisting of methyl alcohol, ethyl alcohol,n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol,t-butyl alcohol, isobutyl alcohol, acetone, methylethyl ketone,diacetone alcohol, ethyl acetate, ethyl lactate, ethylene glycol,diethylene glycol, triethylene glycol, propylene glycol, butyleneglycol, 1,4-butane diol, 1,2,4-butane triol, 1,5-pentane diol,1,2-hexane diol, 1,6-hexane diol, 1,2,6-hexane triol, hexylene glycol,glycerol, glycerol ethoxylate, trimethylolpropane ethoxylate, ethyleneglycol monomethyl ether, ethylene glycol monoethyl ether, diethyleneglycol methyl ether, diethylene glycol ethyl ether, diethylene glycolmethyl ether, diethylene glycol ethyl ether, triethylene glycolmonomethyl ether, triethylene glycol monoethyl ether, 2-pyrrolidone,N-methyl-2-pyrrolidone, caprolactam, dimethyl sulfoxide, tetramethylenesulfone, and thioglycol.
 7. The ink composition according to claim 2,further including at least one of: a viscosity adjuster, a surfactant, astorage stabilizer, and a wetting agent.
 8. The ink compositionaccording to claim 7, wherein the viscosity adjuster includes at leastone of: polyvinyl alcohol, casein, and carboxymethylcellulose.
 9. Theink composition according to claim 8, wherein an amount of the viscosityadjuster is in a range of 0.1-5.0 parts by weight with respect to 100parts by weight of a total weight of the 2-methoxy phenol derivative,the aqueous medium, and the colorant.
 10. The ink composition accordingto claim 7, wherein the surfactant is one of: an anionic surfactant, acationic surfactant and a nonionic surfactant.
 11. The ink compositionaccording to claim 10, wherein an amount of the surfactant is in a rangeof 0.1-5.0 parts by weight with respect to 100 parts by weight of theink composition.
 12. The ink composition according to claim 7, whereinthe wetting agent of the ink composition includes at least one of:polyhydric alcohols, in particular, glycerin, ethylene glycol,diethylene glycol, triethylene glycol, propylene glycol, dipropyleneglycol, hexylene glycol, 1,3-butanediol, 1,4-butanediol,1,5-pentanediol, 1,2-hexanediol, 1,6-hexanediol, 2-butene-1,4-diol,2-methyl-2-pentanediol, and a mixture of the foregoing alcohols.
 13. Theink composition according to claim 12, wherein an amount of the wettingagent is in a range of 2-40 parts by weight with respect to 100 parts byweight of the total weight of 2-methoxy phenol derivative, an aqueousmedium, and a colorant.
 14. The ink composition according to claim 2,wherein the colorant includes a disperse dye or pigment.
 15. The inkcomposition according to claim 14, wherein the disperse dye is at leastone of: DISPERSE YELLOW 3, DISPERSE YELLOW 54, DISPERSE YELLOW 82,DISPERSE RED 60, DISPERSE RED 375, DISPERSE VIOLET 17, DISPERSE RED 4,DISPERSE RED 11, DISPERSE BLUE 60, DISPERSE BLUE 359, DISPERSE BLUE 14,DISPERSE BLUE 3, DISPERSE BLUE 72, and DISPERSE BLUE
 56. 16. The inkcomposition according to claim 14, wherein the pigment is at least oneof: carbon black, graphite, vitreous carbon, activated charcoal,activated carbon, anthraquinone, phthalocyanine blue, phthalocyaninegreen, diazos, monoazos, pyranthrones, perylene, quinacridone, andindigoid pigments.
 17. The ink composition according to claim 2, whereinan amount of the colorant is in a range of 0.1-20 parts by weight withrespect to 100 parts by weight of the ink composition.
 18. The inkcomposition according to claim 2, wherein an amount of the colorant isin a range of 0.5-15 parts by weight with respect to 100 parts by weightof the ink composition.
 19. The ink composition according to claim 14,further including an acid or a base to increase solubility of thedisperse dye in a solvent and stabilize the dispersion of the pigment.20. The 2-methoxyphenol derivative of formula (1) of claim 1, whereinthe 2-methoxyphenol derivative is one of: a toner composition, a paint,and a coating solution.
 21. The ink composition of claim 2, wherein the2-methoxyphenol derivative has a formula of (4):


22. The ink composition of claim 2, wherein the 2-methoxyphenolderivative has a formula of (5):


23. The ink composition of claim 2, wherein the 2-methoxyphenolderivative has a formula of (6):


24. The ink composition of claim 2, wherein the 2-methoxyphenolderivative has a formula of (8):


25. The ink composition of claim 2, wherein the 2-methoxyphenolderivative has a formula of (9):


26. The ink composition of claim 2, wherein the 2-methoxyphenolderivative has a formula of (10):


27. The ink composition of claim 2, wherein the 2-methoxyphenolderivative has a formula of (12):


28. The ink composition of claim 2, wherein the 2-methoxyphenolderivative has a formula of (13):


29. The ink composition of claim 2, wherein the 2-methoxyphenolderivative has a formula of (15):


30. The ink composition of claim 2, wherein the 2-methoxyphenolderivative has a formula of (17):


31. The ink composition of claim 2, wherein the 2-methoxyphenolderivative has a formula of (19):


32. The ink composition of claim 2, wherein the 2-methoxyphenolderivative has a formula of (21):


33. The ink composition of claim 2, wherein the 2-methoxyphenolderivative has a formula of (23):


34. The ink composition of claim 2, wherein the 2-methoxyphenolderivative has a formula of (24):